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Simon, Meike; Karaghiosoff, Konstantin; Knochel, Paul (2018): Diastereoselective intramolecular Carbolithiations of Stereodefined Secondary Alkyllithiums Bearing a Remote Alkynylsilane. In: Organic Letters, Vol. 20, No. 12: pp. 3518-3521
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Various secondary alkyl iodides bearing a remote alkynylsilane underwent intramolecular carbolithiations triggered by an I/Li-exchange performed at -100 degrees C using t-BuLi (2.5 equiv). The resulting alkenyllithiums were stereo selectively converted to tetrasubstituted cyclopentane exo-alkylidenes. After Pd-catalyzed hydrogenation, cyclopentanes and cis-bicyclo[4.3.0]nonanes were obtained with stereo control of four contiguous centers.